Synthesis and antifungal activity of C-21 steroids with an aromatic D ring

Six analogues of salpichrolides with a simplified side chain (6-11) were synthesized using a new methodology to obtain steroids with an aromatic D-ring. The key step was the elimination of HBr in a vicinal dibromo D-homosteroid by treatment with 1,4-diazabicyclo[2.2.2]octane (DABCO). All new compoun...

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Autores principales: Sonego, Juan Manuel, Cirigliano, Adriana Mónica, Cabrera, Gabriela Myriam, Burton, Gerardo, Veleiro, Adriana Silvia
Publicado: 2013
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Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v78_n7_p644_Sonego
http://hdl.handle.net/20.500.12110/paper_0039128X_v78_n7_p644_Sonego
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spelling paper:paper_0039128X_v78_n7_p644_Sonego2023-06-08T15:03:22Z Synthesis and antifungal activity of C-21 steroids with an aromatic D ring Sonego, Juan Manuel Cirigliano, Adriana Mónica Cabrera, Gabriela Myriam Burton, Gerardo Veleiro, Adriana Silvia Antifungal activity Aromatic D-ring DABCO Salpichrolides steroid antifungal activity aromatic D ring article drug structure drug synthesis Fusarium Fusarium solani Fusarium virguliforme nonhuman Antifungal Agents Ergosterol Fusarium Molecular Structure Steroids Fusarium solani Fusarium virguliforme Six analogues of salpichrolides with a simplified side chain (6-11) were synthesized using a new methodology to obtain steroids with an aromatic D-ring. The key step was the elimination of HBr in a vicinal dibromo D-homosteroid by treatment with 1,4-diazabicyclo[2.2.2]octane (DABCO). All new compounds were completely characterized by 2D NMR techniques and tested on two fungal pathogenic species, Fusarium virguliforme and Fusarium solani. © 2013 Elsevier Ltd. All rights reserved. Fil:Sonego, J.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Cirigliano, A.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Cabrera, G.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Veleiro, A.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2013 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v78_n7_p644_Sonego http://hdl.handle.net/20.500.12110/paper_0039128X_v78_n7_p644_Sonego
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Antifungal activity
Aromatic D-ring
DABCO
Salpichrolides
steroid
antifungal activity
aromatic D ring
article
drug structure
drug synthesis
Fusarium
Fusarium solani
Fusarium virguliforme
nonhuman
Antifungal Agents
Ergosterol
Fusarium
Molecular Structure
Steroids
Fusarium solani
Fusarium virguliforme
spellingShingle Antifungal activity
Aromatic D-ring
DABCO
Salpichrolides
steroid
antifungal activity
aromatic D ring
article
drug structure
drug synthesis
Fusarium
Fusarium solani
Fusarium virguliforme
nonhuman
Antifungal Agents
Ergosterol
Fusarium
Molecular Structure
Steroids
Fusarium solani
Fusarium virguliforme
Sonego, Juan Manuel
Cirigliano, Adriana Mónica
Cabrera, Gabriela Myriam
Burton, Gerardo
Veleiro, Adriana Silvia
Synthesis and antifungal activity of C-21 steroids with an aromatic D ring
topic_facet Antifungal activity
Aromatic D-ring
DABCO
Salpichrolides
steroid
antifungal activity
aromatic D ring
article
drug structure
drug synthesis
Fusarium
Fusarium solani
Fusarium virguliforme
nonhuman
Antifungal Agents
Ergosterol
Fusarium
Molecular Structure
Steroids
Fusarium solani
Fusarium virguliforme
description Six analogues of salpichrolides with a simplified side chain (6-11) were synthesized using a new methodology to obtain steroids with an aromatic D-ring. The key step was the elimination of HBr in a vicinal dibromo D-homosteroid by treatment with 1,4-diazabicyclo[2.2.2]octane (DABCO). All new compounds were completely characterized by 2D NMR techniques and tested on two fungal pathogenic species, Fusarium virguliforme and Fusarium solani. © 2013 Elsevier Ltd. All rights reserved.
author Sonego, Juan Manuel
Cirigliano, Adriana Mónica
Cabrera, Gabriela Myriam
Burton, Gerardo
Veleiro, Adriana Silvia
author_facet Sonego, Juan Manuel
Cirigliano, Adriana Mónica
Cabrera, Gabriela Myriam
Burton, Gerardo
Veleiro, Adriana Silvia
author_sort Sonego, Juan Manuel
title Synthesis and antifungal activity of C-21 steroids with an aromatic D ring
title_short Synthesis and antifungal activity of C-21 steroids with an aromatic D ring
title_full Synthesis and antifungal activity of C-21 steroids with an aromatic D ring
title_fullStr Synthesis and antifungal activity of C-21 steroids with an aromatic D ring
title_full_unstemmed Synthesis and antifungal activity of C-21 steroids with an aromatic D ring
title_sort synthesis and antifungal activity of c-21 steroids with an aromatic d ring
publishDate 2013
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v78_n7_p644_Sonego
http://hdl.handle.net/20.500.12110/paper_0039128X_v78_n7_p644_Sonego
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